It has been known that, for example, esters of haloalkenylcyclopropanecarboxylic acids and 2-methyl-4-oxo-3-(2-propynyl)-cyclopent-2-enyl alcohol have an insecticidal activity, see GB-2055822-A.
Application of such compositions containing the above esters, however, is often unavoidably limited not only by their controlling effect but also by their safety, depending on the application conditions. In particular, usually, compositions for controlling pest for preventing epidemics are used mainly in a limited space in a living environment and hence are required to have a desirable insecticidal or repellent activity as well as a marked harmlessness to mammals such as human beings, livestock and pets.
In recognition of the situation, the present inventors have earnestly investigated and consequently found that a specific optically active trans-form of 2-methyl-4-oxo-3-(2-propynyl)-cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2, 2-dimethylcyclopropanecarboxylate is a compound excellent in controlling effect on pest and harmlessness to mammals, to accomplish the present invention.
Thus, the present invention relates to (S)-2-methyl-4-oxo-3-(2-propynyl)-cyclopent-2-enyl (1R)-trans-3-(2,2-dichlorovinyl)-2, 2-dimethylcyclopropanecarboxylate (hereinafter referred to as the present compound) represented by the formula: 
and a composition for controlling pest containing the present compound as an active ingredient.
The present compound can be produced, for example, by reacting (S)-2-methyl-4-oxo-3-(2-propynyl)-cyclopent-2-enyl alcohol (hereinafter referred to as the alcohol compound) represented by the formula: 
with (1R)-trans-3-(2,2-dichlorovinyl)-2, 2-dimethylcyclopropanecarboxylic acid (hereinafter referred to as the carboxylic acid compound) represented by the formula: 
or a reactive derivative (e.g. acid halide or acid anhydride) of said carboxylic acid compound.
The reaction is usually carried out in a solvent in the presence of a condensing agent or a base.
The condensing agent includes, for example, dicyclohexylcarbodiimide (DCC) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (WSC).
The base includes, for example, organic bases such as triethylamine, pyridine, N,N-diethylaniline, 4-dimethylaminopyridine and diisopropylethylamine.
The solvent includes, for example, hydrocarbons such as benzene, toluene and hexane; ethers such as diethyl ether, and tetrahydrofuran; and halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane.
The reaction time ranges usually from 5 minutes to 72 hours.
The reaction temperature ranges usually from xe2x88x9220xc2x0 C. to +100xc2x0 C. (or from xe2x88x9220xc2x0 C. to the boiling point of the solvent in the case where the boiling point of the solvent is lower than +100xc2x0 C.), preferably from xe2x88x925xc2x0 C. to +100xc2x0 C. (or from xe2x88x925xc2x0 C. to the boiling point of the solvent in the case where the boiling point of the solvent is lower than +100xc2x0 C.).
Although the molar ratio of the carboxylic acid compound or its reactive derivative to the alcohol compound can be selected without any limitation, it is preferable to carry out the reaction by using them in an approximate molar ratio of 1:1.
The condensing agent or the base can be used in an arbitrary ratio to the alcohol compound, and is preferably used in an amount of 1 mole to 5 moles per mole of the alcohol compound.
The present compound can be obtained by subjecting the reaction solution after completion of the reaction to conventional after-treatments such as extraction with an organic solvent and concentration. If necessary, it can be further purified by conventional operations such as chromatography, distillation and recrystallization.
The alcohol compound can be produced according to, for example, the process disclosed in U.S. Patent No. 4,571,436, etc. The carboxylic acid compound can be produced according to, for example, the process disclosed in JP-A-4-234991, etc.
Examples of pests on which the present compound has controlling effect are the arthropods given below. Because the present compound can be used as an active ingredient of a composition for controlling the following arthropods and in particular is superior in safety factor, it is especially effective as the active ingredient of a composition for controlling pest for preventing epidemics, which is required to have a high safety to mammals.
Lepidoptera
Pyralidae (pyralid moths) such as Chilo suppressalis (rice stem borer), CnaDhalocrocis medinalis (rice leafroller) and Plodia interpunctella (Indian meal moth); Noctuidae such as Spodoptera litura (tobacco cutworm), Pseudaletia separata (rice armyworm) and Mamestra brassicae (cabbage armyworm); Pieridae such as Pieris rapae crucivora (common cabbageworm); Tortricidae (tortricid moths) such as Adoxophyes spp.; Carposinidae; Lyonetiidae (lyonetiid moths); Lymantriidae (tussock moths); Antographa spp.; Acrotis spp. such as Agrothis segetum (turnip cutworm) and Agrothis ipsilon (black cutworm); Helicoverpa spp.; Heliothis spp.; Plutella xylostella (diamondback moth); Parnara guttata (rice skipper); Tinea translucens (casemaking clothes moth); Tineola bisselliella (webbing clothes moth); Plodia interpunctella (Indian meal moth); etc.
Diptera
Culex spp. such as Culex pipiens pallens (common mosquito)and Culex tritaeniorhvnchus; Aedes spp. such as Aedes aegypti and Aedes albopictus; Anopheles spp. such as Anopheles sinensis; Chironomidae (midges); Muscidae such as Musca domestica (housefly), Muscina stabulans (false stablefly) and Fannia canicularis (little housefly); Calliphoridae; Sarcophagidae; Anthomyiidae (anthomylid flies) such as Delia platura (seedcorn maggot) and Delia antigua (onion maggot); Tephritidae (fruit flies); Drosophilidae (small fruit flies, vinegar flies); Psychodidae (moth flies, sand flies); Simuliidae (black flies); Tabanidae; Stomoxyidae (stable flies); biting midges; etc.
Dictyoptera
Blattella germanica (German cockroach), Periplaneta fuliginosa (smokybrown cockroach), Periplaneta americana (American cockroach), Periplaneta brunnea (brown cockroach), Blatta orientalis (oriental cockroach), etc. Hymenoptera
Formicidae (ants); Vespidae (hornets); Bethylidae (bethylid wasps); Tenthredinidae (sawflies) such as Athalia rosae ruficornis (cabbage sawfly); etc.
Siphonaptera
Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, etc.
Anoplura
Pediculus humanus, Phthirus pubis, etc.
Isoptera Termites
Reticulitermes spereratus, Coptotermes formosanus (Formosan subterranean termite), etc.
Acarina (Mites and Ticks)
Pyroglyphidae such as Dermatophagoides farinae and Dermatophagoides pteronyssinus; Acaridae such as Tyrophagus putrescentiae Schrank (mold mite, copra mite, forage mite) and Aleurogalyphus ovatus Troupeau (brown legged grain mite); Glycyphagidae such as Glycyphagus privatus, Glycyphagus domesticus and Glycyphagus destructor Schrank (groceries mite); Cheyletidae such as Cheyletus malaccensis and Cheyletus moorei; Tarsonemidae; Chrtoglyphus; Oribatei; Tetranychidae (spider mites) such as Tetranychus urticae (two-spotted spider mite), Tetranvchus kanzawai (Kanzawa spider mite), Panonychus citri (citrus red mite) and Panonychus ulmi (European red mite); Ixodidae such as Haemaphysalis longicornis; etc.
Hemiptera
Delphacidae (planthoppers) such as Laodelphax striatellus (small brown planthopper), Nilaparvata lugens (brown planthopper) and Sogatella furcifera (white-backed rice planthopper); Deltocephalidae (leaf-hoppers) such as Nephotettix cincticeps (green rice leafhopper) and Nephotettix virescens (green rice leafhopper); Aphididae (aphids); Pentatomidae (bugs); Aleyrodidae (whiteflies); Coccidae (scales); Tingidae (lace bugs); Psyllidae (psyllids); etc.
Coleoptera
Attagenus unicolor; Anthrenus verbasci (varied carpet beetle); corn rootworms such as Diabrotica virgifera (western corn rootworm) and Diabrotica undecimpunctaca howardi (southern corn rootworm); Scarabaeidae (scarabs) such as Anomala cuprea (cupreous chafer) and Anomala rufocuprea (soybean beatle); Curculionidae (weevils) such as Sitophilus zeamais (maize weevil), Lissorhoptrus oryzophilus (ricewater weevil), Anthonomus grandis grandis (boll weevil) and Callosobruchus chinensis (adzuki bean weevil); Tenebrionidae (darkling beetles) such as Tenebrio molitor (yellow mealworm) and Tribolium castaneum (red fluor beetle); Chrysomelidae (corn rootworms) such as Oulema oryzae (rice leaf beetle), Phyllotreta striolata (striped flea beetles) and Aulacophora femoralis (cucurbit leaf beetle); Anobiidae; Epilachna spp. such as Henosepilachna vigintioctopunctata (twenty-eight-spotted ladybirds); Lyctidae (powder post beetles); Bostrychidae (false powder post beetles); Cerambycidae; Paederus fuscipes (robe beetle); etc.
Thysanoptera (Thrips)
Thrips palmi, Thrips hawaiiensis (flower thrips), etc.
Orthoptera
Gryllotalpidae (mole crickets), Acrididae (grasshoppers), etc.
In the present invention, the composition for controlling pest is for controlling arthropods such as insects and/or acarines.
When the present compound is used as an active ingredient of the composition for controlling pest, it is applied usually after having been formulated into various formulations, for example, oil formulations; emulsifiable concentrates; wettable powders; flowable concentrates such as aqueous suspension concentrates and aqueous emulsion concentrates; granules; dusts; aerosols; heating fumigants such as mosquito coils, electric mosquito mats and solutions for heating fumigation using an absorbent wick; heating smoking formulations such as self-burning-type smoking formulations, chemical-reaction-type smoking formulations and electrically heating-type smoking formulations using a porous ceramic plate; non-heating volatile formulations such as resin volatile formulations and impregnated paper volatile formulations; foggings; ULV formulations; poisonous baits; or the like, usually by mixing the present compound or a solution thereof with a solid carrier, liquid carrier, gaseous carrier, base material for poisonous bait or base material for mosquito coil, and optionally adding auxiliaries for formulation such as surfactants, or alternatively by impregnating a base material such as a mosquito coil or mat with the present compound or a solution thereof.
These formulations usually contain the present compound as an active ingredient in an amount of 0.001 to 95% by weight.
The solid carrier used for formulation includes, for example, fine powders and granules of inorganic carriers such as clays (e.g. kaolin clay, diatomaceous earth, synthetic hydrated silicon dioxide, bentonite, fubasami clay and acid clay), talcs, ceramics, sericite, quartz and calcium carbonate; synthetic resins such as polyethylenes and polypropylenes; and carriers obtained from plants such as wood powder and activated carbon. The liquid carrier includes, for example, water, alcohols (e.g. methanol, ethanol and higher alcohols), ketones (e.g. acetone and methyl ethyl ketone), aromatic hydrocarbons (e.g. benzene, toluene, xylene, ethylbenzene and methylnaphthalene), aliphatic hydrocarbons (e.g. hexane, cyclohexane, kerosene and light oil), esters (e.g. ethyl acetate and butyl acetate), nitriles (e.g. acetonitrile and isobutyronitrile), ethers (e.g. diisopropyl ether and dioxane), acid amides (e.g. N,N-dimethylformamide and N,N-dimethylacetamide), halogenated hydrocarbons (e.g. dichloromethane, trichloroethane and carbon tetrachloride), dimethyl sulfoxide and vegetable oils (e.g. soybean oil and cotton seed oil). The liquefied gas carrier includes, for example, fluorocarbon, fluorohydrocarbon, LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide.
The surfactant includes, for example, alkyl sulfates, alkylsulfonates, alkylarylsulfonates, alkyl aryl ethers and their polyoxyethylenated products, polyethylene glycol ethers, polyhydric alcohol esters and sugar alcohol derivatives.
The auxiliaries for formulation such as adhesive agents and dispersants include, for example, casein, gelatin, polysaccharides (e.g. starch powder, gum arabic, cellulose derivatives and alginic acid), lignin derivatives, bentonite, saccharides and synthetic water-soluble polymers [e.g. poly(vinyl alcohol)s, poly(vinylpyrrolidone)s and poly(acrylic acid)s]. Examples of stabilizer are PAP (acidic isopropyl phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, surfactants and fatty acids or their esters.
Base materials for the mosquito coils include, for example, mixtures of vegetable powders (e.g. wood powder and Pyrethrum marc) and binders (e.g. Tabu powder, starch and gluten).
Base materials for electric mosquito mats include, for example, plates obtained by coagulating fibrils of cotton linter or a mixture of cotton linter and pulp.
Base materials for self-burning-type smoking formulations include, for example, combustible and heat-generating agents (e.g. nitrates, nitrites, guanidine salts, potassium chlorate, nitrocellulose, ethylcellulose and wood powder), pyrolysis-promoting agents (e.g. alkali metal salts, alkaline earth metal salts, dichromates and chromates), oxygen-supplying agents (e.g. potassium nitrate), combustion-supporting agents (melamine and wheat starch), extending agents (e.g. diatomaceous earth) and binders (e.g. synthetic pastes).
Base materials for the chemical-reaction-type smoking formulations include, for example, heat-generating agents (e.g. sulfides, polysulfides, hydrosulfides and hydrate salts of alkali metals, and calcium oxide), catalysts (e.g. carbonaceous substances, iron carbide and activated clay), organic foaming agents (e.g. azodicarbonamide, benzenesulfonylhydrazide, dinitrosopentamethylenetetramine, polystyrenes and polyurethanes) and fillers (e.g. natural fiber pieces and synthetic fiber pieces).
Base materials for the non-heating volatile formulations include, for example, thermoplastic resins, filter papers and Japanese papers.
The base material for poisonous baits includes, for example, bait components (e.g. cereal flour, vegetable oils, saccharides and crystalline cellulose), antioxidants (e.g. dibutylhydroxytoluene and nordihydroguaiaretic acid), preservatives (e.g. dehydroacetic acid), agents for preventing consumption by children or pets (e.g. red pepper powder), and attractants (e.g. cheese perfume, onion perfume and peanut oil).
The flowable concentrates (aqueous suspension concentrates or aqueous emulsion concentrates) usually comprise the present compound, a dispersant, a suspension assistant (e.g. a protective colloid or a compound capable of imparting thixotropic properties), suitable auxiliaries (e.g. defoaming agents, rust preventives, stabilizers, spreaders, penetration assistants, anti-freezing agents, bactericides and fungicides) and water. The protective colloid includes, for example, gelatin, casein, gums, cellulose ether and poly(vinyl alcohol)s. The compound capable of imparting thixotropic properties includes, for example, bentonite, aluminum magnesium silicate, xanthan gum and poly(acrylic acid)s. It is also possible to prepare an oil-based suspension concentrate by using an oil substantially incapable of dissolving the present compound, in place of water.
The formulations thus obtained are applied as they are or after diluted with water or the like, depending on the purposes.
It is also possible to apply the formulations in admixture or combination with other insecticides, acaricides, repellents, synergists or the like.
The insecticides and acaricides include, for example, organophosphorus compounds such as Fenitrothion [O,O-dimethyl O-(3-methyl-4-nitrophenyl)phosphorothioate], Fenthion[O,O-dimethyl O-(3-methyl-4-(methylthio)phenyl)-phosphorothioate], Diazinon [O,O-diethyl O-2-isopropyl-6-methylpyrimidin-4-ylphosphorothioate], Chlorpyrifos[O,O-diethyl O-3,5,6-trichloro-2-pyridylphosphorothioate], Acephate[O,S-dimethylacetylphosphoramidothioate], methidathion[S-2,3-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3-ylmethyl O,O-dimethylphosphorodithioate], Disulfoton[O,O-diethyl S-2-ethylthioethyl-phosphorodithioate], DDVP [2,2-dichlorovinyldimethyl phosphate], Sulprofos [O-ethyl O-4-(methylthio)phenyl S-propylphosphorodithioate], Cyanophos [O-4-cyanophenyl O,O-dimethylphosphorothioate], Dioxabenzophos [2-methoxy-4H-1,3,2-benzodioxaphosphorine-2-sulfide], Dimethoate [O,O-dimethyl S-(N-methylcarbamoylmethyl) dithiophosphate], Phenthoate [ethyl 2-dimethoxyphosphinothioylthio-(phenyl)acetate], Malathion [diethyl (dimethoxy-phosphinothioylthio)succinate], Trichlorfon [dimethyl 2,2,2,-trichloro-l-hydroxyethylphosphonate], Azinphosmethyl [S-3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-ylmethyl O,O-dimethylphosphorodithioate], Monocrotophos [dimethyl (E)-1-methyl-2-(methylcarbamoyl)vinylphosphate] and Ethion [O,O,Oxe2x80x2,Oxe2x80x2-tetraethyl S,Sxe2x80x2-methylenebis(phosphoro-dithioate)]; carbamate type compounds such as BPMC [2-sec-butylphenylmethylcarbamate], Benfuracarb [ethyl N-[2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl(methyl)-aminothio]-N-isopropyl-xcex2-alaninate], Propoxur [2-isopropoxyphenyl N-methylcarbamate], Carbosulfan [2,3-dihydro-2,2-dimethyl-7-benzo[b]furanyl N-dibutylaminothio-N-methylcarbamate], Carbaryl [1-naphthyl-N-methyl-carbamate], Methomyl [S-methyl-N-[(methylcarbamoyl)oxy] thioacetimidate], Ethiofencarb [2-(ethylthiomethyl)-phenylmethylcarbamate], Aldicarb [2-methyl-2-(methylthio)propionaldehyde O-methycarbamoyloxime], Oxamyl [N,N-dimethyl-2-methylcarbamoyloxyimino-2-(methylthio)acetamide] and Phenothiocarb [(S-4-phenoxybutyl)-N,N-dimethylthiocarbamate]; pyrethroid compounds such as Etofenprox [2-(4-ethoxyphenyl)-2-methylpropyl-3-phenoxybenzyl ether), Fenvalerate [(RS)-xcex1-cyano-3-phenoxybenzyl (RS)-2-(4-chlorophenyl)-3-5 methylbutyrate], Esfenvalerate [(S) -xcex1-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate], Fenpropathrin [(RS)-xcex1-cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclo-propanecarboxylate], Cypermethrin [(RS)-xcex1-cyano-3-phenoxybenzyl (1RS)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], Permethrin [3-phenoxybenzyl (1RS)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], Cyhalothrin [(RS)-xcex1-cyano-3-phenoxybenzyl (Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate], Deltamethrin [(S) -xcex1-cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate], Cycloprothrin [(RS)-xcex1-cyano-3-phenoxybenzyl (RS)-2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylate], Fluvalinate [xcex1-cyano-3-phenoxybenzyl N-(2-chloro-xcex1, xcex1, xcex1-trifluoro-p-tolyl)-D-valinate], Bifenthrin [(2-methylbiphenyl-3-ylmethyl) (Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate], 2-methyl-2-(4-bromodifluoromethoxyphenyl)propyl (3-phenoxybenzyl) ether, Tralomethrin [(S)-xcex1-cyano-3-phenoxybenzyl (1R-cis)3 {(1RS)-(1,2,2,2-tetrabromoethyl) }-2,2-dimethylcyclopropanecarboxylate], [4-ethoxyphenyl{3-(4-fluoro-3-phenoxyphenyl)propyl} dimethylsilane], d-Phenothrin [3-phenoxybenzyl (1R-cis,trans)-chrysanthemate], [(RS)-xcex1-cyano-3-phenoxybenzyl (1R-cis,trans)-chrysanthemate], d-Resmethrin [5-benzyl-3-furylmethyl (1R-cis,trans)-chrysanthemate], [(S) -xcex1-cyano-3-phenoxybenzyl (1R-cis(Z))-(2,2-dimethyl-3- {3-oxo-3-(1,1,1,3,3, 3-hexafluoropropyloxy)propenyl} cyclopropanecarboxylate], Cyfluthrin [(RS)-xcex1-cyano-4-fluoro-3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], Tefluthrin [2,3,5,6-tetrafluoro-4-methylbenzyl (1RS-cis(Z))-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2, 2-dimethylcyclopropanecarboxylate], Transfluthrin [2,3,5,6-tetrafluorobenzyl (1R-trans)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], Tetramethrin [3,4,5,6-tetrahydrophthalimidomethyl (1RS)-cis,trans-chrysanthemate], Allethrin [(RS)-3-allyl-2-methyl-4-oxocyclopent-2-enyl (1RS)-cis,trans-chrysanthemate], Prallethrin [(S)-2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl (1R)-cis,trans-chrysanthemate], Empenthrin [(RS)-1-ethynyl-2-methyl-2-pentenyl (1R)-cis,trans-chrysanthemate], Imiprothrin [2,5-dioxo-3-(prop-2-ynyl)imidazolidin-1-ylmethyl (1R)-cis,trans-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate], d-Flamethrin [5-(2-propynyl)furfuryl (1R)-cis,trans-chrysanthemate], and 5-(2-propynyl)furfuryl 2,2,3,3-tetramethylcyclopropane-carboxylate]; N-cyanoamidine derivatives such as N-cyano-Nxe2x80x2-methyl-Nxe2x80x2-(6-chloro-3-pyridylmethyl)acetoamidine; chlorinated hydrocarbon compounds such as Endosulfan [6,7,8,9,10,10-hexachloro-1,5,5a, 6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepin oxide], xcex3-BHC [1,2,3,4,5,6-hexachlorocyclohexane], 1,1-bis(chlorophenyl)-2,2,2-trichloroethanol; benzoylphenylurea type compounds such as Chlorfluazuron [1-(3,5-dichloro-4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)phenyl)-3-(2,6-difluorobenzoyl)urea], Teflubenzron [1-(3,5-dichloro-2,4-difluorophenyl)-3-(2, 6-difluorobenzoyl)urea], [1-(4-(2-chloro-4-trifluoromethylphenoxy)-2-fluorophenyl)-3-(2,6-difluorobenzoyl)urea]; thiourea derivatives such as [N-(2,6-diisopropyl-4-phenoxyphenyl)-Nxe2x80x2-tert-butylcarbodi-imide]; phenylpyrazole type compounds; Metoxadiazon [5-methoxy-3-(2-methoxyphenyl)-1, 3,4-oxadiazol-2-(3H)-one], Bromopropylate [isopropyl 4,4xe2x80x2-dibromobenzilate]; Tetradifon [4-chlorophenyl 2,4,5-trichlorophenylsulfone]; Quinomethionate [S,S-6-methylquinoxaline-2,3-diyldithiocarbonate]; Pyridaben [2-tert-butyl-5-(4-tert-butylbenzylthio)-4-chloropyridazin-3(2H)-one]; Fenpyroximate [tert-butyl(E)-4-[(1,3-dimethyl-5-phenoxypyrazol-4-yl)methyleneaminoxymethyl] benzoate]; [N-4-tert-butylbenzyl)-4-chloro-3-ethyl-1-methyl-5-pyrazolecarboxamide]; Polynactin complexes [tetranactin, dinactin and trinactin]; Pyrimidifen [5-chloro-N-[2-{4-(2-ethoxyethyl)-2,3-dimethylphenoxyl} ethyl]-6-ethylpyrimidine-4-amine]; Milbemectin; Abamectin; ivermectin; azadirachtin [AZAD]; etc.
The repellents include, for example, 3,4-caranediol, N,N-diethyl-m-toluamide, 1-methylpropyl 2-(2-hydroxyethyl)-l-piperidinecarboxylate, p-menthane-3,8-diol, and plant essential oils such as hyssop oil.
The synergists include, for example, bis-(2,3,3,3-tetrachloropropyl) ether (S-421), N-(2-ethylhexyl)bicyclo-[2.2.1]hept-5-ene-2,3-dicarboximide (MGK-264), and xcex1-[2-(2-butoxyethoxy)ethoxy]-4,5-methylenedioxy-2-propyltoluene (piperonyl butoxide).
When the present compound is used as an active ingredient of a composition for controlling pest for preventing domestic epidemics or for controlling pest for animals, formulations in the form of emulsifiable concentrates, wettable powders or flowable concentrates are applied usually after having been diluted with water so that the formulations have a concentration of the present compound falling within the range of from 0.1 to 10,000 ppm. Formulations in the form of oil formulations, aerosols, fumigants, smoking formulations, volatile formulations, foggings, ULV formulations, poisonous baits or resin formulations are applied as they are.
Both the applying dosage and the applying concentration of the above formulations can be properly determined depending on conditions such as the type of formulation, when, where and how these formulations are applied, kind of pests, degree of damage, etc.